Trail running in the Berkshires can be challenging and technical. Kennedy Park, in the heart of Lenox, offers a great alternative, with its  smooth, runnable trails, well maintained by a team of volunteers. There is a nice, approximately 4.5 mile loop starting at the Arcadian Shop off Route 20 (also a great resource for maps, trail information, and coffee!). Park here and follow the trails along the ridge for about 2 miles until reaching Reservoir Road. From there, loop back northeast on the Loghop trail, which will bring you back to the starting point. There are good options for a longer run, but bring a map — the park can be a labyrinth if you don’t know your way! Note the trails are also open to horses and mountain bikes, so be aware of others and follow protocol for who yields to whom.

Additional Option: We’ve mapped out a loop through Lenox to Tanglewood. Pleasant roads, and then enjoy a jaunt around the gorgeous grounds at Tanglewood.

Lenox & Tanglewood Loop
  • 4.5 mile loop; Options for more
  • Gently hilly
  • Arcadian Shop, Rt. 20 Lenox
  • Park at the Arcadian Shop.